A Fool's Love
by Wings Over Wealth
Summary: Was once called Not Gonna Let you Go and was planned to be written RiddlerInTime. Good!Ron Badboy!TomRiddle Nerd!Harry. Your kind of typical love between bad boy and nerd. Tom makes a bet on dating Harry, the socially awkward nerd. Tom asks Harry out, and somehow Harry already knows what's going on. So why is he doing this? 5 comments new chap.
1. Step 1: Introduction to Target

Ok, so I planned to actually just have this as a plot bunny for anyone. RiddlerInTime had tried to write said bunny but was unfortunately stopped. So I suppose I'm writing this too. Probably gonna write this as another comments = chapter sort of thing

Enjoy this little...prologue of sorts

Title: A Fool's Love

Author: Wings over Wealth

Rating: T

Pairing: TM/HP

summary...well yea...

Disclaimer: I DON'T OWN HARRY POTTER! NOPE NOT AT ALL!

* * *

"HEY NERD! GET OUT OF THE WAY!" A shrieking horn rang loud and clear as Harry Potter dashed towards the school like a rabbit. His messy black mop of hair tapped against his glasses as he hugged the text books tight to his chest and rushed inside.

His heart beat violently at the fear that had he not moved he would have… he sighed and secretively pinched the back of his hand, reminding himself to think of the living, not the dead.

"Harry!" There was only one voice that would sound so…there was no way to explain it except simply saying Hermione Granger, aka Ms. Know-it-all. "Did you finish the Latin report?" Harry nodded mutely, and she raised an eyebrow, "And the History essay?" He sighed, almost rolling his eyes, and nodded once more, "Did you study for the Chem Test then?" He hesitated, just for a second, and Hermione began the talk. "Harry! What have I told you about studying?! Especially for Chemistry?! Professor Snape doesn't like you as it is and the fact that you would dare to try to get out of this-"

"I got it, 'Mione. I just fell asleep last night on accident." Harry winced as his words seemed to ring down the hall. Luckily, there was too much noise that it was drowned out by everything else.

Her eyes seemed to soften at his expression, "Harry, were you-?"

The raven pressed a firm hand over her mouth, "No, we don't talk about my personal life in school. You promised."

Hermione sighed, "Alright, fine. But people are going to find out some time…"

Just as Harry was about to retort, a head of red hair nudged his back. "Hey mate, Hermione acting like a mother hen again?"

Hermione huffed as an arm slung around Harry's neck. Ronald Weasley was the youngest red head son of the Weasley family and supposedly the best at rugby in the school, heading to state championships and all.

"At least Harry spends some time on his homework." Hermione lectured.

"Well, I focus on athletics, something that's useful, unlike all that information your big head."

"Oh yeah? Like you can remember anything beside the location of those playboy magazines of yours?"

Ron sputtered, "I-I-"

"Look, let's just get going." Harry finally cut in. "We're going to be late for English." He gripped both their hands and raced down the hall.

They didn't even notice a certain group staring at them as they dashed away.

* * *

Prologue: DONE

Let's go with 5 comments as a starter. I still need to finish chapter's for the other stories too.

Review, favorite, follow. Thank you for reading and I hope you enjoyed!

~Wings Over Wealth


	2. Step 2: Set the Bet

Let me clear this up first. These are the definitions of a bad boy and a nerd in this story.

Anyway, I'm amazed that I got 13 reviews for this! So I'm posting the first actual chapter. This time, 7 reviews and I'll continue.

Main Pairing: TMR/HP

Side pairings: Ron/Hermione, Theodore/Draco, Blaise/Seamus, TMR/Ginny (one-sided), James/Lily (dead)

* * *

Tom Riddle is what people considered a perfect human, a prodigy. He had an attitude the size of Canada (second to the attitude of Draco Malfoy which was the size of Russia), although he'd refuse to admit it. Saying it was just the pride that came with his perfect abilities, well…

He's an all-out jerk, and everybody adored him, fawned over him, or became enamored with him.

Harry isn't considered part of that "everyone".

All his friends knew he was gay, that included his family relations. And quite frankly, they were fine with it ("As long I can snog you." Seamus Finnegan had said flirtatiously and was then instantly punched in the stomach by his best friend, Dean Thomas.) Well, some of them were. But many thought that he'd fallen for Tom Riddle, just because he's gorgeous and perfect, that everyone should love him.

"Honestly, what's not to like about him?" Seamus sighed, looking off dreamily. "He's drop-dead gorgeous, smart, funny, awesome. He's a bad boy, and he's bi. If I didn't have Dean, I would have grabbed him and never let go." Considering it was study hall, Ron, Hermione, Seamus and Harry sat close to one another with Ron and Harry in front and Seamus and Hermione in the back; Each taking up a chair before sitting. None of the other students even paid attention to the group as they were called "the losers" and were considered the lowest on the chain of popularity. Not that they cared, really. Ron was the only one that used to be popular. Now that he was always around his girlfriend, Hermione, people looked to him less often and he'd become one of them.

Although Harry was now Ron's best friend, he still remembered a time when Harry wouldn't even dare to talk to him. Hermione had told him that Harry was just like that, shy and quiet...that is until he got used to Ron. After a while, the quiet, shy boy that once was became a funny, kind, and cunning soul in the body of a small boy, making him all the more devilish.

"You're lucky your boyfriend isn't here right now." Harry grumbled. He was trying very hard nowadays to keep his temper in check around Tom, whom insulted him left and right. What would he give to manage outwitting Tom? A lot. The only problem was his voice. It took him quite a while to stop mumbling around Ron, and even though he knew everyone in the school, he still talked quietly subconsciously which didn't allow for his comebacks and retorts to sound all that great.

Seamus pouted, "I don't consider that lucky. Since I don't have one, I can only wank to some gay porn. I even bought a couple of toys but-" Harry rolled his eyes. He knew that Seamus was just doing this to tease Ron, possibly the most innocent mind left in the group that Seamus hadn't corrupted...yet. Of course, Harry, feeling a bit sadistic to Ron at the moment, allowed Seamus to continue to ramble about his sex toys and porn.

Ron covered his ears whilst blushing bright red, "Oook, too much information. Hermione, how can you stand to listen to this pervert?" He looked over to his girlfriend whom somehow managed to keep a straight face despite the conversation.

"…Hmm? What was that?" Hermione pulled one of the earplugs from her ears. "Ron? Did you say something?"

Oh, that's how she managed.

"Nevermind that." Harry finally interrupted, feeling that Ron has had enough torture for the hour. "Where's Parvati and Lavender? It's not like them to skip study hall."

"They're not exactly skipping, more like 'putting it to better use'." Seamus made air quotes with his fingers. "They're probably somewhere getting coffee or shopping."

"They only have 5 minutes left; do you think they're going to make it in by the bell?" Ron asked, taking the book from Hermione's hands and kissing her forehead when she scowled at him.

Harry and Seamus shared a grin. "Not a chance."

* * *

"Hey look," Draco Malfoy pointed out from his seat next to the Blaise Zabini and Theodore Nott. "Tom's dumping another one."

Blaise looked over with interest before sighed with disappointment. "Not my taste," He briefly scanned the room, pausing in the corner of the cafeteria before quickly going back to fiddling with...Well, I'm not quite sure what he's fiddling with, but I'm certain it's important...to someone.

Theodore snorted, "'Course she's not your taste, your taste run into coffee and sex twenty four-seven." It was true, the teen drank about two liters of coffee a day, and said to be able to have a hard-on all day and every day.

Blaise glared. "Shut up" he grumbled and subtly glanced over at a table across the room, comfortably placed in a corner. There sat Seamus Finnegan and his friends. Really, Seamus was all that mattered in Blaise's view. The Irish boy was adorable, and possibly the cutest person out there that he knew, so much that he could be put on par with those kitten commercials. He couldn't help how much he was attracted to the boy, not that he would ever tell him of course. Ever.

While he continued to watch Seamus like a...stalker? No...whatever, anyways...Theo began to inspect the crying girl as Tom walked over. "Who's the girl?"

Tom stared at him strangely. "I have no idea."

Theo and the blonde stared at him, wide-eyed. "How long did you go out with her?"

The raven shrugged, "Two weeks? Something like that? She was a good lay but bitched about everything, so annoying." All he could feel for her was irritation and the satisfaction of sex. He really didn't care, he's had better than her and prettier than her too. He's dated both men and women, but always to get out the aggression he'd felt in himself.

When Tom had turned 6, he was often beaten by his drunken mother. Considering how his father had left her, there was a number of ways it could have gone, his mother chose the wrong one. It was her coping mechanism, but it was his bane. And he ran away from home at the age of 9, after 3 years of abuse.

He was placed in an orphanage and was bounced from place to place until he landed with the father he had now. He was friendly, very supportive of his sexuality and everything; wanted children despite being single and so adopted Tom. They knew he was hurt, deeply and that there was no way to ever change that hurt, but they tried their hardest to be his family. He knew that, but there was no way that he could ever grow close to anyone anymore. It just...couldn't happen.

"So...who's next?" Tom walked a slight in front of Theo and Draco, with Blaise quietly trailing behind before disappearing entirely. He scanned the crowds in the hall as they all rushed for their next class.

"Right," Draco sighed, picking at his nails. "Well, what this time?"

"...Guy, I'm in the mood for it." Draco rolled his eyes.

"Why do I even do this for you?"

Tom smirked. "Because everybody loves me." Suddenly he was bumped by something small, knocking it to the ground.

"I'm sorry." A small voice mumbled. Tom found his ears straining to hear the voice and sneered when he figured out who it was. His red eyes glared at the raven on the ground

"Potter." He hissed. The other boy was groping around for his glasses.

Upon finding them and setting them straight on his face, Harry looked up and gave Tom a look at those soft black lashes and vivid green eyes. "Riddle." His eyes narrowed the same way Tom's did.

"Still a loser there, Potter?"

Harry growled quietly, grumbling a few words. His anger slowly rising as his hands shook while holding his textbooks. He shoved past them and stormed off.

"What'd you say, Potter? I can't hear you." Tom taunted after him before stalking off the other way.

Theo and Draco watched the interaction a little ways off, not speaking a word. They didn't quite understand why Riddle would hate the boy so much. When asked, Tom had simply said, "He sets my teeth on edge." and refused to answer anymore questions. They had met Harry on their own, without Tom around and he seemed quite nice, a tad shy perhaps, but polite and friendly. He was also smaller than the rest of the teens his age, even smaller than almost all of the girls. Maybe that's why his friends were so protective of him, afraid that he would break at a moment's notice.

As they continued their thought process, they didn't notice their friend's sudden stop in front of them and bumped into his back. Startled, they looked around to stare at his face only to notice his face changed into a vilified smile. "I got an idea."

"Ohh no...I'm almost afraid to ask." Theo covered his eyes in mock horror.

Tom glared at him, but continued to smile. Nothing could spoil his good mood. "I need to get myself a date with Potter."

...

The silence that answered him had him grinning even wider than before.

"...I'm sorry, can you run that by me again?" Draco said, pretending to clean out his ears while Theo kept pinching his arm to make sure it wasn't a dream.

"Dating Potter." Tom simplified.

"But don't you hate him?" Theo questioned.

"Yeah, which is why breaking him will feel so much better than just sex." Tom smiled. He felt the delight and glee bubble up inside at the thought. Draco felt an entirely different feeling inside.

Guilt.

"I'd give my new car to you before he'd ever let you do him." Theo laughed. Draco felt the feeling begin to curl inside his gut.

"It's a bet" Tom replied, nonchalantly.

_Just you wait, Potter. __Just you wait._

They never noticed the blue eyes that followed them as they sat down.

* * *

_YEAAAAAAAAAAAAAAAAAAAAAAAA I'M DONE THE FIRST CHAPTER._

7 comments for the next chap.

Once again, review, favorite, follow. Thank you for reading and I hope you enjoyed!

~Wings Over Wealth


	3. Step 3: Planning from Both Sides

7 comments: THANK YOU.

Enjoi your reading!

* * *

"How is Ron?" Hermione asked through the computer, clearly concerned for her friend. Harry just sighed and shrugged, flicking his pencil shavings at the red head who was writing furiously trying to finish the report for the next day.

Harry was staying over at Ron's again for the third time that week. His aunt had apologized constantly for this and while Harry had not minded, he also proposed he stay at home to help Dudley. Aunt Petunia refused, claiming that she would constantly worry had it only been her two boys at home with no one to protect them.

Harry's birth parents, James and Lily Potter, had died in a car crash with a drunk driver. He was then sent to live with his last living relatives, Petunia and Vernon Dursley and their son/ his cousin, Dudley Dursley. At the time, Harry had just turned 1 year old and was two years younger than his cousin. Petunia's motherly instincts had kicked in and Dudley had loved the idea of a new playmate. Vernon, however, was angered at the idea of taking the child that had absolutely nothing to do with their "perfect" family setting. He didn't fit in Vernon's eyes, and so the fat man decided to insult him and beat him at every turn when he turned 10.

After Harry had been abused by his uncle-in-law for two years or so, his aunt had had enough of the screaming, fighting, and the horrible insults flying around. She lectured both Harry and Vernon, as Dudley had actually tried to help Harry, for fighting and Vernon slapped her in the face, yelling for her to get out. Harry grew angry and stormed out of the house in following his last relative out the door.

Petunia and he found a rather small apartment in which they lived while using Petunia's money which she had hidden from Vernon. The money, however, was not enough to live off; it could only give them five months to find a job. Petunia had managed a job working as a waitress at the local diner, her boss, Mr. Weathersbee was a jolly man who was very fond of her son and Harry and often gave a helping hand to them. Dudley had come after them half a year later, after Petunia had received full custody of her son from the divorce with Vernon.

"I'm sorry, Harry. But I managed to get an extra shift and-"

"It's alright, Aunt Petunia. Dudley called me about it, we'll be staying over at our friends' houses tonight. Don't worry about us, we'll be fine."

"Alright…But if anything-"

"Happens we call you immediately, we know." Harry finished. "Dudley will be staying at Pier's and I'll be staying at Ron's, love you. Bye." He hung up after a small apologetic goodbye and yawned. He had begun to work at the local library in the community in order to work for some money, little as it was, and help out around the house. Dudley had done the same, except he could actually work a job considering his age. Harry's cousin managed a part-time job as an amusement park attendant. They managed through life little by little, and things weren't always the greatest, but it was enough to give them shelter, warmth and food.

Harry had originally stayed over at Hermione's for the most part, but it seemed extremely suspicious to many people that they might have been having a love affair behind Ron's back. Not only that, but Molly Weasley, Ron's mother, had taken a liking to Harry and began to treat him as though he was one of her own, despite how she had six sons already.

"I can always take on a seventh." She replied jovially whenever Ron commented on how she treated Harry.

"Sometimes, I feel like I should be jealous of how she treats you." Ron had stated one day when Harry slept over.

"Are you?" Harry asked calmly, although he was as jumpy as a ball of fire that his friend would hate him now.

"Bloody hell no. I'm glad she's not going all mother hen on _me _anymore. I'm officially passing that baton to you." He mockingly held out his hands in a bow, as though giving someone of royalty their scepter. What was in his hands was a roll of Mentos and Harry raised an eyebrow questioningly.

"Bloody hell no. I'm glad she's not going all mother hen on _me _anymore. I'm officially passing that baton to you." He mockingly held out his hands in a bow, as though giving someone of royalty their scepter. What was in his hands was a roll of Mentos and Harry raised an eyebrow questioningly.

Ron smiled wickedly, "Revenge on the twins. We still have that two liter bottle of Coke no one drank from last month."

"…Your report?" If Ron didn't finish it under Harry's supervision, Hermione was going to tear the two boys to bits.

Ron grew smug. "Finished…somewhat."

Harry's eyes widened before creasing in silent laughter. "Let's get going then…"

* * *

One might wonder how Tom was going to initiate the plan. One might also wonder why Tom had only thought of this plan now.

The two questions can be answered quite easily.

For one, Tom had only just now thought of the plan because of how acutely he noticed the scent of something on Harry as he stormed past him in the hall. The scent of cologne, something that Harry had never worn before, and it made Tom curious. Plus, Tom was losing it, his mojo, his attitude towards sex. Everyone always wanted him, piled at his feet to be his girlfriend or boyfriend, and he was losing the challenge. Tom wanted the taste of a chase, it was so much more fun to have the people falling for him in the process rather than having them already fallen. Like apples are better to be plucked from a tree then picked from the ground, he needed something fresh. And who hated him more than Harry Potter, his mortal enemy? The chase would be fun and the break-up would be so sweet.

For him, that is.

On another note, he wasn't sure how to go about it. Tom was sure Harry had felt something for him, hatred as a front but there was definitely something beneath that. He would ask him out, just to see how it would go. Then, he'd go on from there.

"Tom?" His surrogate father, Johnathan Bones, called, nearing the bottom of the stairs.

"Yes, John?" John had tried to get Tom to call him dad at one point, but had given up when Tom couldn't even fathom to call him "father", accepting the title "John" was hard enough for a boy that didn't even talk to him.

"I was wondering…" John scratched at the back of his head, cracking a nervous smile. "If you'd like to…eat together?" he sighed, running a hand through his mass of salt-and-pepper hair. John worked as a lawyer to Bones Law Firm and was able to charm the pants off anyone in court, yet when faced with his adopted son, he found himself stuttering and nervous.

It's not that Tom was scary to his adoptive father or anything, they were just different and separate. It was strange for Tom to talk about anything really to his father, although John tried hard to get him to speak up.

"...Sure..." Tom shrugged and slid off his bed padding past John and out the door.

It was a silent affair, and tension grew between the two men in the dining room. It didn't take long before John tried to strike up some conversation. "So…How's school?"

Tom rolled his eyes inwardly, such a typical question. "Fine."

"And how's…that girlfriend of yours?"

That one nearly knocked Tom out of his seat. "My girlfriend? How do you know about this?" He was seething with anger. It wasn't that his father found out that he was angry about, it's that someone's been keeping tabs on him that set him on edge. Someone's been following him and _he hadn't even known_, that made him furious.

John was taken aback by the sudden emotion and ferocity in his voice. "I saw you two when I was driving home…You know you can bring your girlfriend around if you want. I don't mind." He smiled politely, but he was absolutely giddy inside. Finally, it was a subject that he could talk about as father-to-son. It's happened to him too, so he can connect with Tom on that level at least; it's a start.

"She's not my girlfriend…" He grumbled, still a little peeved despite knowing the truth.

"You know, Tom. It's alright to tell me if you have a girlfriend…or a boyfriend." He paused before adding. He wasn't sure on his son's sexuality, but he would be supportive no matter what.

"Right, thanks." The last word was mumbled, but John heard it all the same, leaving the older man feeling very satisfied with himself while Tom was anything but.

* * *

"Glucose is made of…Malfoy?" Harry exclaimed, noticing the platinum blond hair that was pacing a hole into the tiled floor in front of the raven's classroom.

Draco looked up and smiled before his eyes saddened and it faded. "Harry! Just the person I was looking for!" He looked around out of paranoia, the school could have been filled with gossip-mongers for all he knew...oh wait, it is.

Harry looked at him curiously. "What? Is something wrong?"

Draco, who'd secretly become good friends with Harry, pulled him into the janitor's closet.

"I need to tell you something…in secret."

"I figured," Harry gasped, startled by the sudden push into the darkness. The single bulb of light flickered on in between them. "Since you shoved me into a closet for it." He fixed his glasses atop his nose.

Draco rolled his eyes at Harry's theatrics. "It's about Tom Riddle."

Harry's eyes narrowed into slits at the name. "What about him?" He hissed.

Draco shook his head almost in pity. "He's made a bet."

Harry looked annoyed. "If that's all, then I don't care." Harry turned around and reached for the doorknob.

"Wait! The bet's about you." The raven whirled around at that, wide eyed.

"…I'm listening?"

"Tom made a bet that he would be able to shag you and then leave you in the dust." Draco pleaded. "I'm sorry, Harry. I just wanted to tell you so you would know beforehand. Especially since-"

Harry held up his hands, "Woah now, Draco. That's in the past. You don't need to worry anymore. But thanks for the info…I'll keep that in mind."

Draco sighed, feeling that he'd done his part, and walked out of the janitor's closet with Harry. Luckily, everyone else had already gone to classes and no one was in the halls. They split into different directions. Harry, walking into his class, sat down with a frown marring his face. It wasn't until later that day that he'd come up with a plan to deal with Tom.

He smiled wickedly at the thought as he headed to the usual lunch table.

"Everyone? I need your help."

* * *

I thank everyone for commenting on the story.

Once again 7 comments and I'll go on.

Hope everyone enjoyed and I'll be off to sleep then. Toodles~

Once again, review, favorite, follow. Thank you for reading and I hope you enjoyed!

~Wings Over Wealth


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